Organic Electric Element

ABSTRACT

The present disclosure relates to an organic electric element for realizing high luminous efficiency, and high heat resistance of the element, improve the color purity of the element, and increase the lifetime of the element.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a divisional of U.S. application Ser. No. 17/604,912filed Oct. 19, 2021, which is a U.S. National Phase application under 35U.S.C. 371 of International Application No. PCT/KR2020/008149, filed onJun. 23, 2020, which claims the benefit of Korean Patent Application No.10-2019-0075219, filed on Jun. 24, 2019. The entire disclosures of theabove applications are incorporated herein by reference. In addition, ifthis patent application claims priority for countries other than theUnited States for the same reason as above, all contents thereof areincorporated into this patent application by reference.

TECHNICAL FIELD

The present disclosure relates to an organic electric element.

BACKGROUND ART

In general, an organic light emitting phenomenon refers to a phenomenonwhere electrical energy is converted into light energy using an organicmaterial. An organic electric element using the organic light emittingphenomenon has a structure including an anode, a cathode, and an organicmaterial layer disposed between the cathode and the anode. Here, in anumber of cases, the organic material layer has a multi-layer structuremade of different materials in order to improve the efficiency andstability of an organic electric element. For example, the organicmaterial layer may include a hole injection layer, a hole transportlayer, an emitting layer, an electron transport layer, an electroninjection layer, and the like.

The materials used in the organic material layer may be categorized asemitting materials and charge transport materials, such as a holeinjection material, a hole transport material, an electron transportmaterial, and an electron injection material, depending on the function.

In addition, the emitting materials may be categorized as high-molecularweight types and low-molecular weight types depending on the molecularweight, and may be categorized as fluorescent materials based on singletexcitation of electrons and phosphorescent materials based on tripletexcitation of electrons depending on the emission mechanism. Inaddition, the emitting materials may be categorized as blue, green, andred emitting materials depending on the color of emitted light, as wellas yellow and orange emitting materials necessary for realizing morenatural colors.

When a single material is used as an emitting material, a maximumemission wavelength may be shifted to a long wavelength and color puritymay decrease because of interactions between molecules, or deviceefficiency may decrease because of an emission quenching effect. Thus, ahost-dopant system may be used as an emitting material in order toincrease color purity and increase luminous efficiency through energytransfer. According to the principle, when a small amount of dopanthaving a smaller energy band gap than the host of the emitting layer isadded to the emitting layer, excitons generated in the emitting layerare transferred to the dopant to generate light with high efficiency. Atthis time, since the wavelength of the host is shifted to the wavelengthband of the dopant, light having an intended wavelength may be obtaineddepending on the type of the dopant used.

Currently, in the portable display market, displays are increasing insize into large-area displays. Since portable displays are provided witha battery serving as a power supply, portable displays require moreefficient consumption power than existing consumption power. Inaddition, in this situation, not only the challenge for efficientconsumption power but also challenges for luminous efficiency andlifetime must be solved.

Efficiency, lifetime, a driving voltage and the like are related to eachother. An increase in the efficiency leads to a relative decrease in thedriving voltage, by which the crystallization of the organic materialdue to Joule heating during driving is reduced, thereby increasing thelifetime. However, simply improving the organic material layer may notmaximize the efficiency. This is because, when the optimal combinationof the energy level and Ti value between each organic material layer andthe intrinsic properties (mobility, interfacial properties, etc.) of thematerial are achieved, both increased life and high efficiency may beachieved. Therefore, it is necessary to develop a light-emittingmaterial that may efficiently achieve charge balance in the emittinglayer while having high thermal stability.

That is, in order to sufficiently exhibit the excellent characteristicsof the organic electric element, materials for forming the organicmaterial layer in the element, such as a hole injection material, a holetransport material, a light-emitting material, an electron transportmaterial, an electron injection material, and an emitting-auxiliarylayer material, should be supported by stable and efficient materials.However, such a stable and efficient organic material layer material foran organic electric element has not been sufficiently developed yet.

Recently, technology for improving color purity and increasingefficiency by optimized optical thickness between an anode and a cathodein a top device with a resonance structure as well as research onimproving device characteristics by giving performance changes of eachmaterial may be one of the important factors to improve the deviceperformance. Compared with the bottom device structure of thenon-resonant structure, the top device structure has a large opticalenergy loss due to surface plasmon polariton (SPP) because the formedlight is reflected by the anode, which is a reflective film, and emittedtoward the cathode.

Therefore, one of the important methods for improving the shape andefficiency of an organic electric element spectral is a method of usinga capping layer for the top cathode. In general, four metals such as Al,Pt, Ag, Au are mainly used for electron emission in the SPP, and thesurface plasmon is generated on the surface of the metal electrode. Forexample, when the cathode is used as the Ag, the light emitted by the Agof the cathode is quenched by the SPP and the efficiency is reduced dueto light energy loss by the Ag.

On the other hand, when the capping layer is used, the SPP is generatedat the interface between the MgAg electrode and the high refractiveorganic material. In this case, TM (transverse magnetic) polarized lightthereof is annihilated on the capping layer surface in the verticaldirection by an evanescent wave and TM polarized light moving along thecathode and the capping layer is amplified by surface plasma resonance,thereby increasing the intensity of the peak and enabling eventuallyhigh efficiency and effective color purity control.

DISCLOSURE Technical Problem

The present disclosure is intended to provide an organic electricelement able to provide excellent luminous efficiency, high heatresistance, high color purity, and increased lifetime.

Technical Solution

According to an aspect, the present disclosure provides An organicelectric element comprising a first electrode; a second electrode; anorganic material layer located between the first electrode and thesecond electrode, and a capping layer disposed on at least one of onesurface of the first electrode opposite to the organic material layerand one surface of the second electrode opposite to the organic materiallayer, wherein the capping layer comprises a compound represented byFormula 1 below.

Advantageous Effects

As set forth above, it is possible to realize excellent luminousefficiency, high heat resistance, high color purity, and increasedlifetime by including a capping layer using the compound according tothe present disclosure.

DESCRIPTION OF DRAWINGS

FIGS. 1 to 3 are cross-sectional views illustrating an organiclight-emitting element according to an embodiment of the presentdisclosure.

MODE FOR INVENTION

Hereinafter, embodiments of the present disclosure will be described indetail with reference to the accompanying drawings.

In designating components of the drawings by reference numerals, thesame components will be designated by the same reference numerals ifpossible although they are shown in different drawings. Further, in thefollowing description of the present disclosure, a detailed descriptionof known functions and configurations incorporated herein will beomitted in the situation in which the subject matter of the presentdisclosure may be rendered unclear thereby. When “includes”, “has”,“consisting of”, etc. mentioned in this specification are used, otherparts may be added unless “only” is used. When a component is expressedin a singular, it may include a case in which the plural is includedunless otherwise explicitly stated.

In addition, terms, such as first, second, A, B, (a), or (b), may beused herein when describing components of the present disclosure. Eachof these terminologies is not used to define an essence, order, orsequence of a corresponding component but used merely to distinguish thecorresponding component from other components.

In the case that it is described that a certain component is“connected”, “coupled”, or “joined” to another component, it should beunderstood that another component may be “connected”, “coupled”, or“joined” to the component not only directly but also indirectly throughan intervening component. Here, other components may be included in oneor more of two or more components that are “connected”, “coupled” or“connected” to each other.

In addition, in the case that it is described that a certain component,such as a layer, a film, an area, or a plate, is “above” or “over”another component, it should be understood that the component may beabove another component not only “directly” but also indirectly throughan intervening component. In contrast, in the case that it is describedthat a certain component is “directly above” another component, itshould be understood that there is no intervening element.

When a temporal precedence or flow precedence relation is describedwith, for example, “after”, “next”, “before”, etc., in the descriptionof the temporal flow relationship related to the components, theoperation method, the manufacturing method, etc., it may include a casewhere it is not continuous unless “immediately” or “directly” is used.

On the other hand, when numerical values or corresponding informationfor components are mentioned, even if there is no separate explicitdescription, the numerical values or the corresponding information maybe interpreted as including an error range that may be caused by variousfactors (e.g., process factors, internal or external shocks, noise,etc.).

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and refers tosaturated aliphatic functional radicals including a straight chain alkylgroup, a branched chain alkyl group, a cycloalkyl (alicyclic) group, analkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkylgroup.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl”, asused herein, includes a halogen-substituted alkyl group.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has a double or triple bond of 2 to 60 carbon atoms and includesa straight chain group or a branched chain group, but is not limitedthereto.

Unless otherwise stated, the term “cycloalkyl” as used herein refers to,but is not limited to, alkyl forming a ring having 3 to 60 carbon atoms.

The term “alkoxy group” or “alkyloxy group”, as used herein, refers toan alkyl group to which an oxygen radical is attached and, unlessotherwise stated, has, but is not limited to, 1 to 60 carbon atoms.

The term “alkenoxyl group”, “alkenoxy group”, “alkenyloxyl group”, or“alkenyloxy group” refers to an alkenyl group to which an oxygen radicalis attached, and unless otherwise stated, has, but is not limited to, 2to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, asused herein, has, but is not limited thereto, 6 to 60 carbon atoms. Inthis specification, the aryl group or the arylene group includes amonocyclic compound, a ring assembly, fused polycyclic systems, a spirocompound, or the like. For example, the aryl group include, but are notlimited to, phenyl, biphenyl, naphthyl, anthryl, indenyl, phenanthryl,triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl,fluoranthenyl, and the like. The naphthyl may include 1-naphthyl and2-naphthyl, and the anthryl may include 1-anthryl, 2-anthryl and9-anthryl.

Unless stated otherwise, the term “fluorenyl group” or “fluorenylenegroup”, as used herein, may refer to a monovalent or divalent functionalgroup of fluorene. In addition, the “fluorenyl group” or “fluorenylenegroup” may refer to a substituted fluorenyl group or a substitutedfluorenylene group. The term “substituted fluorenyl group” or“substituted fluorenylene group”, as used herein, may refer to amonovalent or divalent functional group of substituted fluorene. Theterm “substituted fluorene” may refer to a compound in which at leastone of substituent R, R′, R″, or R′″ below is a functional group otherthan hydrogen, and includes a case in which R and R′ are bonded to forma spiro compound together with carbon atoms attached thereto.

The term “spiro compound”, as used herein, may have a ‘spiro union’, andthe spiro linkage may refer to a linkage made by two rings sharing onlyone atom. At this time, the atoms shared by the two rings may refer to‘spiro atoms’, and they may refer to ‘monospiro-’ compound, ‘dispiro-’compound, compound, ‘trispiro-’ compound depending on the number ofspiro atoms in a compound, respectively.

The term “heterocyclic group”, as used herein, includes not onlyaromatic rings such as “heteroaryl group” or “heteroarylene group” butalso non-aromatic rings, and unless stated otherwise, may refer to aring having 2 to 60 carbon atoms including one or more of hetero atom,but it is not limited thereto. Unless stated otherwise, as used herein,the term “heteroatom” refers to N, O, S, P or Si, and the hetero ringgroup may refer to a monocyclic group including a heteroatom, a ringaggregate, a fused multiple ring system, a spy compound or the like.

In addition, the “heterocyclic group” or “hetero ring group”, as usedherein, may include rings having SO₂ in place of a ring-forming carbonatom. For example, the “heterocyclic group” includes the followingcompound:

The term “ring”, as used herein, refers to monocyclic rings andpolycyclic rings, includes not only hydrocarbon rings but also heterorings including at least one heteroatom, and includes aromatic rings andnon-aromatic rings.

The term “polycyclic ring”, as used herein, includes ring assemblies,such as biphenyl or terphenyl, fused polycyclic systems, and spirocompounds. The polycyclic ring includes not only aromatic compounds butalso non-aromatic compounds, and includes not only hydrocarbon rings butalso hetero rings including at least one heteroatom.

The term “aliphatic ring group”, as used herein, may refer to a cyclichydrocarbon other than an aromatic hydrocarbon, and include a monocyclictype, a ring assemblies, a fused multiple ring system, a spiro compound,and the like, Unless otherwise specified, it may refer to a ring having3 to 60 carbon atoms. For example, even when benzene, which is anaromatic ring, and cyclohexane, which is a non-aromatic ring, are fused,it corresponds to an aliphatic ring.

The term “ring assembly”, as used herein, may refer to a compound inwhich two or more rings (single rings or fused ring systems) are joineddirectly by single or double bonds and in which the number of suchdirect ring junctions is one less than the total number of ring systemsin the compound. In ring assemblies, the same or different ring systemsmay be joined directly by single or double bonds. For example, in thecase of an aryl group, it may be a biphenyl group, a terphenyl group,etc., but it is not limited thereto.

The term “fused polycyclic system”, as used herein, may refer to a formof fused rings sharing at least two atoms. For example, in the case ofan aryl group, it may be a naphthalenyl group, a phenanthrenyl group, afluorenyl group, etc., but it is not limited thereto.

In addition, in the case that prefixes are named consecutively, it meansthat substituents are listed in the order of the prefixes. For example,an aryl alkoxy group refers to an alkoxy group substituted with an arylgroup, an alkoxy carbonyl group refers to a carbonyl group substitutedwith an alkoxy group, and an aryl carbonyl alkenyl group refers to analkenyl group substituted with an arylcarbonyl group, with thearylcarbonyl group being a carbonyl group substituted with an arylgroup.

Unless clearly stated otherwise, the term “substituted” in the term“substituted or non-substituted”, as used herein, may refer tosubstitution with one or more substituents selected from the groupconsisting of, but not limited to, deuterium, a halogen, an amino group,a nitrile group, a nitro group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxygroup, a C₁-C₂₀ alkyl amine group, a C₁-C₂₀ alkylthiophene group, aC₆-C₂₀ arylthiophene group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynilgroup, a C₃-C₂₀ cycloalkyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ arylgroup substituted with deuterium, a C₈-C₂₀ aryl alkenyl group, a silanegroup, a boron group, a germanium group, and a C₂-C₂₀ hetero ring groupincluding at least one heteroatom selected from the group consisting ofO, N, S, Si, and P.

Herein, “the name of a functional group” corresponding to the arylgroup, the arylene group, the hetero ring group, or the like illustratedas each symbol and a substituent thereof may be written in “the name ofthe functional group on which the valence thereof is reflected” or maybe written in “the name of the parent compound thereof”. For example,phenanthrene, i.e., a type of aryl group, may be written in group namesby distinguishing the valence. That is, a monovalent phenanthrene“group” may be written as “phenanthryl (group),” while a divalentphenanthrene “group” may be written as “phenanthrylene (group)”. Incontrast, phenanthrene groups may be written as “phenanthrene”, i.e. thename of the parent compound, regardless of the valence. Similarly,pyrimidine may be written as “pyrimidine” regardless of the valence ormay be written in group names each corresponding to the valence, inwhich a monovalent pyrimidine group is written as pyrimidinyl (group)and a divalent pyrimidine group is written as pyrimidinylene (group).Accordingly, when the type of a substituent is written in the name ofthe parent compound in this specification, the written name may refer toan n-valence “group” formed by the desorption of a carbon atom and/or aheteroatom-bonded hydrogen atom from the parent compound.

In addition, unless clearly stated otherwise, formulas used herein areapplied in the same manner as the definition of the substituent based onthe exponential definition of the following Formula:

Here, when a is 0, there is no substituent R¹. When a is 1, a singlesubstituent R¹ is attached to any one of the carbon atoms of the benzenering. When a is 2 or 3, the substituent R¹ is attached in the followingmanner, where R¹ may be of the same or different values. When a is aninteger between 4 and 6, the substituent R¹ is attached to a carbon atomof the benzene ring in a similar manner. Here, the illustration ofhydrogen atoms attached to carbon atoms of the benzene ring will beomitted.

Herein, the expression “substituents bonded to form a ring” may refer toa case that adjacent groups are bonded to each other to form a singlering or fused multiple rings, and the single ring and the formed fusedmultiple rings may include not only hydrocarbon rings, but also includesheterocycles including at least one heteroatom, and may include aromaticand non-aromatic rings.

The organic electric element, as used herein, may refer to the organiclight emitting diode including the constituent(s) between the anode andthe cathode, or, and the anode, the cathode and the constituent(s)positioned therebetween.

In addition, in some cases, the organic electric element, as usedherein, may refer to an organic light emitting diode and a panelincluding the same, or may refer to an electronic device including thepanel and a circuit. Here, for example, the electronic device includes adisplay device, a lighting device, a solar cell, a portable or mobileterminal (e.g., a smart phone, a tablet, a PDA, an electronicdictionary, a PMP, etc.), a navigation terminal, a game machine, variousTVs, and various computers. It may include all monitors, etc., but it isnot limited thereto, and may be any type of device as long as thecomponent(s) are included.

FIGS. 1 to 3 are cross-sectional views illustrating an organiclight-emitting element according to an embodiment of the presentdisclosure.

An organic electric element according to an embodiment of the presentdisclosure may include a first electrode, a second electrode, an organicmaterial layer positioned between the first electrode and the secondelectrode, and a capping layer disposed on at least one of one surfaceof the first electrode opposite to the organic material layer and onesurface of the second electrode opposite to the organic material layer.

Referring to FIG. 1 , the organic electric element according to theembodiment of the present disclosure, a first electrode 110, a secondelectrode 170, and the organic material layers 120, 130, 140, 150 and160 positioned between the first electrode 110 and the second electrode120 and the capping layer 180, and the capping layer 180 may be locatedon one surface of the second electrode 170 opposite to the organicmaterial layer. In the embodiment shown in FIG. 1 , the capping layer180 is located on one surface of the second electrode 170, but inembodiments of the present disclosure, the capping layer 180 may be alsolocated on one surface of the first electrode 110. When the cappinglayer 180 is positioned on one surface of the first electrode 110, theone surface is one surface opposite to the organic material layer amongthe surfaces of the first electrode 110, so that the capping layer 180may be located in the lower part of the first electrode 110.

The thickness of the capping layer 180 may be 30 nm to 120 nm. The lowerlimit of the thickness of the capping layer 180 may be, for example, 40nm or more, 50 nm or more, or 55 nm or more. The upper limit of thethickness of the capping layer 180 may be, for example, 100 nm or less,80 nm or less, or 65 nm or less. When the thickness of the capping layeris adjusted within the above-described range, it is possible to providethe organic electric element having high luminous efficiency and colorpurity due to the surface plasma resonance.

The capping layer 180 may have a refractive index of 1.85 or more withrespect to light having a wavelength of 450 nm to 750 nm. The upperlimit of the refractive index of the capping layer for the light havinga wavelength of 450 nm to 750 nm is not particularly limited, but maybe, for example, 3.0 or less or 2.5 or less. When the refractive indexof the capping layer is adjusted within the above-described range, it ispossible to provide the organic electric element having high luminousefficiency and color purity due to the surface plasma resonance.

The first electrode 110 shown in FIG. 1 may be an anode and the secondelectrode 170 may be a cathode, and in the case of an inverted type, thefirst electrode is a cathode and the second electrode may be an anode.

The organic material layer may include a hole injection layer 120, ahole transport layer 130, a light emitting layer 140, an electrontransport layer 150, and an electron injection layer 160. Specifically,the hole injection layer 120, the hole transport layer 130, the lightemitting layer 140, the electron transport layer 150, and the electroninjection layer 160 may be sequentially disposed on the first electrode110.

In addition, referring to FIG. 2 , in the organic electric element 200according to another embodiment of the present disclosure, the holeinjection layer 220 and the hole transport layer sequentially disposedon the first electrode 210 230, a buffer layer 243, a light emittingauxiliary layer 253, a light emitting layer 240, an electron transportlayer 250, an electron injection layer 260, a second electrode 270, anda capping layer 280. In the embodiment shown in FIG. 2 , the cappinglayer 280 is positioned on one surface of the second electrode 270, butin embodiments of the present disclosure, the capping layer 280 islocated on one surface of the first electrode 210. When the cappinglayer 280 is positioned on one surface of the first electrode 210, theone surface is one surface opposite to the organic material layer amongthe surfaces of the first electrode 210, so that the capping layer 280may be located in the lower part of the first electrode 210.

Meanwhile, although not shown in FIG. 2 , an electron transportauxiliary layer may be further disposed between the light emitting layer240 and the electron transport layer 250.

In addition, referring to FIG. 3 , the organic electric element 300according to another embodiment of the present disclosure may be thattwo or more stacks ST1 and ST2 of multi-layered organic material layersmay be disposed between the first electrode 310 and the second electrode370. For example, the first stack ST1 is disposed on the first electrode310, the second stack ST2 is disposed on the first stack ST1, the secondelectrode 370 is disposed on the second stack ST2, and the capping layer380 may be disposed on the second electrode 370. A charge generatinglayer CGL may be disposed between the first stack ST1 and the secondstack ST2. In the embodiment shown in FIG. 3 , the capping layer 380 ispositioned on one surface of the second electrode 370, but inembodiments of the present disclosure, the capping layer 380 is locatedon one surface of the first electrode 310. When the capping layer 380 ispositioned on one surface of the first electrode 310, the one surface isone surface of the first electrode 310 opposite to the organic materiallayer, so that the capping layer 380 may be located in the lower part ofthe first electrode 310.

Specifically, the organic electric element 300 includes the firstelectrode 310, the first stack ST1, the charge generating layer CGL, thesecond stack ST2, and the second electrode 370 and the capping layer380.

The first stack ST1 is an organic material layer formed on the firstelectrode 310, which includes a first hole injection layer 321, a firsthole transport layer 331, a first light emitting layer 341 and the firstelectron transport layer 351. The second stack ST2 may include a secondhole transport layer 332, a second emitting layer 342, and a secondelectron transport layer 352. Additionally, an electron injection layer360 may be included between the second electrode and the second electrontransport layer. As such, the first stack and the second stack may be anorganic material layer having the same stacked structure.

The charge generating layer CGL may include a first charge generatinglayer 390 and a second charge generating layer 391. The chargegenerating layer CGL is disposed between the first and second lightemitting layers 341 and 342, thereby increasing the efficiency of acurrent generated in each of the light emitting layers and may play arole of smoothly distributing charges.

For example, the first emitting layer 341 may include a light emittingmaterial including a blue fluorescent dopant in a blue host, and thesecond emitting layer 342 includes a material doped with both a greenishyellow dopant and a red dopant in a green host, but the material of thefirst and second light emitting layers 341 and 342 according to anembodiment of the present disclosure is not limited thereto.

The charge generating layer CGL and the second stack ST2 may berepeatedly positioned n times where n is a positive integer. Forexample, n may be an integer of 1 to 5. For example, when n is 2, thecharge generating layer CGL and the third stack may be further stackedon the second stack ST2.

The capping layers 180, 280, and 380 may be disposed on one surfaceopposite to the organic material layer among the surfaces of the firstelectrode 110, 210, 310 and one surface opposite to the organic materiallayer among the surfaces of the second electrode 170, 270, 370 in theFIGS. 1-3 , When the capping layer is disposed thereon, the lightefficiency of the organic electric element may be improved. For example,when the capping layer is positioned below the first electrodes 110,210, and 310 or above the second electrodes 170, 270, 370, light emittedthrough the electrodes is emitted from the capping layer having arelatively high refractive index. As it passes through, the wavelengthof light is amplified and the luminous efficiency may be increased.

In the case of a top emission organic light emitting element, thecapping layers 180, 280, 380 may play a role in reducing optical energyloss due to the surface plasmon polaritons (SPPs) in the secondelectrodes 170, 270, 370. In the case of a bottom emission organicelectric element, the capping layers 180, 280, and 380 may serve as abuffer for the second electrodes 170, 270, and 370.

On the other hand, when a plurality of light-emitting layers are formedby a multi-layer stack structure method as shown in FIG. 3 , the organicelectric element that emits white light by the mixing effect of lightemitted from each light-emitting layer can be manufactured.

An organic light emitting element according to an embodiment of thepresent disclosure may be fabricated using a variety of depositionmethods. The organic light emitting element may be fabricated using adeposition method, such as physical vapor deposition (PVD) or chemicalvapor deposition (CVD). For example, the organic light emitting elementmay be fabricated by: forming the anodes 110, 210, and 310 by depositinga metal, a conductive metal oxide or an alloy thereof on a substrate,forming the organic material layer including the hole injection layers120, 220 and 321, the hole transport layers 130, 230 331 and 332, thelight emitting layers 140, 240, 341 and 342, the electron transportlayers 150, 250, 351 and 352, and the electron injection layer 160, 260and 360 thereon, and depositing a material used as the cathodes 170,270, and 370 thereon.

In addition, the organic material layer may be fabricated into a smallernumber of layers by a solution process or a solvent process, such as aspin coating process, a nozzle printing process, an inkjet printingprocess, a slot coating process, a dip coating process, a roll-to-rollprocess, a doctor blading process, a screen printing process, or athermal transfer process, using a variety of polymer materials. Sincethe organic material layer according to the present disclosure may beformed by a variety of methods, the scope of the right of the presentdisclosure is not limited by the method forming the organic materiallayer.

The organic electric element according to the present disclosure may bea top emission type, a bottom emission type, or a dual emission typedepending on the material used therein.

The white organic light-emitting device (WOLED) has merits, such as theease of realization of high resolution, superior process ability, andthe ability thereof to be fabricated using existing color filtertechnologies for liquid crystal displays (LCDs). For the WOLED mainlyused in a backlight unit, a variety of structures have been proposed andpatented. Representative are a planar side-by-side arrangement of red(R), green (G), and blue (B) light-emitting structures, a vertical stackarrangement of RGB light-emitting structures, and a color conversionmaterial (CCM) structure in which electroluminescence from a blue (B)organic emitting layer and photo-luminescence from an inorganicluminescent material using the electroluminescence are used. The presentdisclosure may be applied to the WOLED.

In embodiments of the present disclosure, the hole injection layers 120,220 and 321, the hole transport layers 130, 230, 331 and 332, the bufferlayer 243, the light emission auxiliary layer 253, the electrontransport layers 150, 250, 351 and 352, the electron injection layers160, 260 and 360, the light emitting layers 140, 240, 341 and 342, orthe capping layers 180, 280 and 380 may include the compoundsrepresented by the Formula 1 below. For example, the capping layers 180,280 and 380 may include a compound represented by the Formula 1 below.

Hereinafter, the compound according to the aspect of the presentdisclosure is represented by the Formula 1 below.

The substituents and linking groups described in the Formula 1 will bedescribed as follows.

Ar¹ to Ar⁴ may be each independently selected from a group consisting ofa C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ hetero ring group comprising at least oneheteroatom selected from among O, N, S, Si, or P; and a fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring.

For example, Ar¹ to Ar⁴ may be each independently selected from a groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; and a C₂-C₆₀hetero ring group comprising at least one heteroatom selected from amongO, N, S, Si, or P.

When Ar¹ to Ar⁴ are respectively an aryl group, each of Ar¹ to Ar⁴ maybe independently a C₆-C₆₀ aryl group, a C₆-C₄₀ aryl group, C₆-C₂₅ arylgroup, or a C₆-C₁₀ aryl group. In this case, Ar¹ to Ar⁴ may be the sameas or different from each other.

When Ar¹ to Ar⁴ are respectively a hetero ring group, each of Ar¹ to Ar⁴may be a C₂-C₆₀ hetero ring group, a C₂-C₄₀ hetero ring group or aC₂-C₂₀ hetero ring group. In this case, Ar¹ to Ar⁴ may be the same as ordifferent from each other.

At least one of Ar¹ to Ar⁴ is represented by formula 1-1.

L¹ and L² may be each independently selected from a group consisting ofa single bond; a C₁-C₅₀ alkylene group; a C₂-C₂₀ alkenylene group;C₆-C₆₀ arylene group; fluorenylene group; a C₂-C₆₀ hetero ring groupcomprising at least one heteroatom selected from among O, N, S, Si, orP; and a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring.

When L¹ and L² are respectively an arylene group, each of L¹ and L² maybe independently a C₆-C₆₀ arylene group, a C₆-C₄₀ arylene group, aC₆-C₂₅ arylene group, or C₆-C₁₀ arylene group. In this case, L¹ and L²may be the same as or different from each other.

When L¹ and L² are respectively a hetero ring group, each of L¹ and L²may be a C₂-C₆₀ hetero ring group, a C₂-C₄₀ hetero ring group or aC₂-C₂₀ hetero ring group. In this case, L¹ and L² may be the same as ordifferent from each other.

L³ to L⁶ may be each independently selected from a group consisting of asingle bond; a C₁-C₅₀ alkylene group; a C₂-C₂₀ alkenylene group; C₆-C₆₀arylene group; fluorenylene group; a C₂-C₆₀ hetero ring group comprisingat least one heteroatom selected from among O, N, S, Si, or P; and afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring.

When L³ to L⁶ are respectively an arylene group, each of L³ to L⁶ may beindependently a C₆-C₆₀ arylene group, a C₆-C₄₀ arylene group, a C₆-C₂₅arylene group, or C₆-C₁₀ arylene group. In this case, L³ to L⁶ may bethe same as or different from each other.

When L³ to L⁶ are respectively a hetero ring group, each of L³ to L⁶ maybe a C₂-C₆₀ hetero ring group, a C₂-C₄₀ hetero ring group or a C₂-C₂₀hetero ring group. In this case, L³ to L⁶ may be the same as ordifferent from each other.

R¹ and R² may be each independently selected from the group consistingof deuterium; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₆-C₆₀aryl group; a fluorenyl group; a C₂-C₆₀ hetero ring group comprising atleast one heteroatom selected from among O, N, S, Si, or P; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and-L′-N(R_(a))(R_(b)), and one or more adjacent R¹s are the same ordifferent and a plurality of R¹s are bonded to form a ring and one ormore adjacent R²s are the same or different and a plurality of R²s arebonded to form a ring.

For example, R¹ and R² may be each independently selected from the groupconsisting of deuterium; a C₆-C₆₀ aryl group; a fluorenyl group; and aC₂-C₆₀ hetero ring group comprising at least one heteroatom selectedfrom among O, N, S, Si, or P.

When R¹ and R² are respectively an aryl group, each of R¹ and R² may beindependently a C₆-C₆₀ aryl group, a C₆-C₄₀ aryl group, a C₆-C₂₅ arylgroup, or a C₆-C₁₀ aryl group. In this case, R¹ and R² may be the sameas or different from each other.

When R¹ and R² are respectively a hetero ring group, each of R¹ and R²may be a C₂-C₆₀ hetero ring group, a C₂-C₄₀ hetero ring group or aC₂-C₂₀ hetero ring group. In this case, R¹ and R² may be the same as ordifferent from each other.

R³ may be selected from the group consisting of deuterium; a C₁-C₅₀alkyl group; a C₂-C₂₀ alkenyl group; a C₆-C₆₀ aryl group; a fluorenylgroup; a C₂-C₆₀ hetero ring group comprising at least one heteroatomselected from among O, N, S, Si, or P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; and -L′-N(R_(a))(R_(b)) andone or more adjacent R³s are the same or different and a plurality ofR³s are bonded to form a ring.

For example, R³ may be each independently selected from the groupconsisting of deuterium; a C₆-C₆₀ aryl group; a fluorenyl group; and aC₂-C₆₀ hetero ring group comprising at least one heteroatom selectedfrom among O, N, S, Si, or P.

When R³ is respectively an aryl group, each of R³ may be independently aC₆-C₆₀ aryl group, a C₆-C₄₀ aryl group, a C₆-C₂₅ aryl group, or a C₆-C₁₀aryl group. In this case, a plurality of R³s R²s are the same ordifferent.

When R³ are respectively a hetero ring group, each of R³ may be a C₂-C₆₀hetero ring group, a C₂-C₄₀ hetero ring group or a C₂-C₂₀ hetero ringgroup. In this case, a plurality of R³s R²s are the same or different.

a and b may be each independently an integer of 0 to 3.

c may be an integer of 0 to 4, and when two or more of Ar¹ to Ar⁴ may berepresented by the formula 1-1, a plurality of c's may be the same ormay be different.

L′ may be each independently selected from a group consisting of asingle bond; C₆-C₆₀ arylene group; fluorenylene group; a C₂-C₆₀ heteroring group comprising at least one heteroatom selected from among O, N,S, Si, or P; and a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring.

R_(a) and R_(b) may be each independently selected from a groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heteroring group comprising at least one heteroatom selected from among O, N,S, Si, or P; and a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring.

X may be O or S.

Ring A may be each independently a C₆-C₃₀ aryl group, a C₆-C₂₅ arylgroup or a C₆-C₁₀ aryl group. The ring A is an aryl group satisfying theabove carbon number range, and may be an aryl group fused to asubstituent represented by the Formula 1-1. For example, the ring A maybe each independently selected from the group consisting of benzene,naphthalene, phenanthrene, and anthracene.

Y may be each independently CR^(a)R^(b) or NR^(c), and when Y is bondedto the formula 1, it may be N or C. when Y may be plural, a plurality ofYs may be the same or may be different.

Y′ may be each independently N, O or S.

R^(a), R^(b) and R^(c) may be each independently hydrogen; deuterium; aC₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ hetero ring group comprising at least oneheteroatom selected from among O, N, S, Si, or P; and a fused ring groupof a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; or combinationsthereof.

When R^(a), R^(b) and R^(c) are respectively an aryl group, each ofR^(a), R^(b) and R^(c) may be independently a C₆-C₆₀ aryl group, aC₆-C₄₀ aryl group, C₆-C₂₅ aryl group, or a C₆-C₁₀ aryl group. In thiscase, R^(a), R^(b) and R^(c) may be the same as or different from eachother.

When R^(a), R^(b) and R^(c) are respectively a hetero ring group, eachof R^(a), R^(b) and R^(c) may be a C₂-C₆₀ hetero ring group, a C₂-C₄₀hetero ring group or a C₂-C₂₀ hetero ring group. In this case, R^(a),R^(b) and R^(c) may be the same as or different from each other.

-   -   adjacent L¹ and R¹ may be bonded to form a ring.    -   adjacent L¹ and Ar¹ may be bonded to form a ring.    -   adjacent L¹ and Ar² may be bonded to form a ring.    -   adjacent L¹ and L³ may be bonded to form a ring.    -   adjacent, L¹ and L⁴ may be bonded to form a ring.    -   adjacent L² and R² may be bonded to form a ring.    -   adjacent L² and Ar³ may be bonded to form a ring.    -   adjacent L² and Ar⁴ may be bonded to form a ring.    -   adjacent L² and L⁵ may be bonded to form a ring.    -   adjacent L² and L⁶ may be bonded to form a ring.

In Ar¹ to Ar⁴, L¹ to L⁶, R¹ to R³, R^(a) and R^(b), each of the arylgroup, the fluorenyl group, the hetero ring group, the fused ring group,alkyl group, the alkenyl group, the alkylene group, the arylene groupand the fluorenylene group may be further substituted with one or moresubstituents selected from a group consisting of deuterium; a nitrogroup; a nitrile group; a halogen group; an amino group; a C₁-C₂₀alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; a C₂-C₂₀alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; a C₆-C₂₀aryl group substituted with deuterium; a fluorenyl group; a C₂-C₂₀hetero ring group; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ aryl alkyl group;and a C₈-C₂₀ aryl alkenyl group. Accordingly, when Ar¹ to Ar⁴, L¹ to L⁶,R¹ to R³, R_(a) and R_(b) are understood as primary substituents, theadditionally substituted substituents may be understood as secondarysubstituents.

the additionally substituted substituents as the secondary substituentsmay be bonded to form a ring, and each of the substituents is furthersubstituted with one or more substituents selected from a groupconsisting of deuterium; a nitro group; a nitrile group; a halogengroup; an amino group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group;a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted with deuterium; afluorenyl group; a C₂-C₂₀ hetero ring group; a C₃-C₂₀ cycloalkyl group;a C₇-C₂₀ aryl alkyl group; and a C₈-C₂₀ aryl alkenyl group, and thesubstituents are allowed to be bonded to form a ring. The additionallysubstituted substituents from the second substituents may be understoodas third substituents.

L¹ to L⁶ may be any one of Formulas a-1 to a-13 below.

The substituents of the Formulas a-1 to a-13 are as follows.

Z is O, S, CR^(d)R^(e) or NR^(f), and when Z is bonded to the Formula 1,it may be N or C.

R^(d), R^(e) and R^(f) are each independently selected from the groupconsisting of hydrogen; deuterium; a C₁-C₅₀ alkyl group; a C₂-C₂₀alkenyl group; a C₆-C₆₀ aryl group; fluorenyl group; a C₂-C₆₀ heteroring group and a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring fusedring group comprising at least one heteroatom of O, N, S, Si and P.

When R^(d), R^(e) and R^(f) are an aryl group, for example, the arylgroup is a C₆-C₆₀ aryl group, a C₆-C₄₀ aryl group, a C₆-C₂₅ aryl group,or a C₆-C₁₀ aryl group, and R^(d), R^(e) and R^(f) may be the same as ordifferent from each other.

When R^(d), R^(e) and R^(f) are a hetero ring group, for example, thehetero ring group is a C₂-C₆₀ hetero ring group, a C₂-C₄₀ hetero ringgroup, or a C₂-C₂₀ hetero ring group and R^(d), R^(e) and R^(f) may bethe same as or different from each other.

a″, c″, d″, and e″ may be each independently an integer of 0 to 4, andb″ may be an integer of 0 to 6.

f″ and g″ may be each independently be an integer of 0 to 3, h″ may bean integer of 0 to 2, and i″ may be an integer of 0 or 1.

R⁷ to R⁹ are each independently selected from the group consisting ofdeuterium; C₆-C₆₀ aryl group; fluorenyl group; a C₂-C₆₀ hetero ringgroup containing at least one heteroatom selected from the groupconsisting of O, N, S, Si and P, and may be bonded to form a ring.

When R⁷ to R⁹ is an aryl group, for example, the aryl group is a C₆-C₆₀aryl group, a C₆-C₄₀ aryl group, a C₆-C₂₅ aryl group, or a C₆-C₁₀ arylgroup, and R⁷ to R⁹ may be the same as or different from each other.

When R⁷ to R⁹ is a hetero ring group, for example, the hetero ring groupis a C₂-C₆₀ hetero ring group, a C₂-C₄₀ hetero ring group, or a C₂-C₂₀hetero ring group and R⁷ to R⁹ may be the same as or different from eachother.

Z⁴⁹, Z⁵⁰, and Z⁵¹ may each independently be CR′ or N, and at least oneof Z⁴⁹, Z⁵⁰, and Z⁵¹ may be N.

R′ is each independently selected from the group consisting of hydrogen;deuterium; C₆-C₆₀ aryl group; fluorenyl group; a C₂-C₆₀ hetero ringgroup comprising at least one heteroatom selected from the groupconsisting of O, N, S, Si and P, and may be bonded to form a ring.

When R′ is an aryl group, for example, R′ may be a C₆-C₆₀ aryl group, aC₆-C₄₀ aryl group, a C₆-C₂₅ aryl group, or a C₆-C₁₀ aryl group, and R′may be the same as or different from each other.

When R′ is a hetero ring group, for example, R′ may be a C₂-C₆₀ heteroring group, a C₂-C₄₀ hetero ring group, or a C₂-C₂₀ hetero ring group,and R′ may be the same as or different from each other.

The compound represented by the Formula 1 is represented by one offollowing Formulas 1-A to 1-T.

where Ar¹ to Ar⁴, R¹ to R³, L¹ to L⁶, a, b, c, X, Y and Y′ in theFormulas 1-A to 1-T are the same as defined in the Formula 1, and R⁴ toR⁶ are the same as R¹ as defined in the Formula, d is an integer from 0to 5, e is an integer from 0 to 2, f is an integer from 0 to 3, and aplurality of d's, e's f's are the same as or different from each other.

At least one of Ar¹ to Ar⁴ may be represented by the following Formulas1-1a to 1-e.

In the Formulas 1-1a to 1-1e, R³ and c are the same as defined inFormula 1.

The compound represented by the Formula 1 comprises one of followingcompounds, but it is not limited thereto.

The compound included in each of the capping layer and the organicmaterial layer may be a single compound or two or more types ofcompounds having different structures.

For example, in the organic material layer, two types of compoundshaving different structures from among the above-described compounds maybe mixed at a mole ratio of from 99:1 to 1:99.

Synthesis examples of the compound represented by the Formula 1 andfabrication examples of the organic electric element according toembodiments of the present disclosure will be described in detailhereinafter, but the present disclosure is not limited thereto.

SYNTHESIS EXAMPLES

The compound (or final products) represented by Formula 1 according tothe present disclosure is synthesized by reacting Sub 1 and Sub 2 as inReaction Scheme 1 below but is not limited thereto. In the ReactionScheme 1 below, X, L¹ to L⁶, Ar¹ to Ar⁴, R¹, R², a, and b are the sameas those described above regarding Formula 1, and Hal¹ is Br, Cl or I.

However, if the amino group of Sub 1 is the same as Sub 2, the finalproduct may be directly synthesized through Sub 1a and Sub 2

Synthesis Example of Sub 1

Sub 1 of the Reaction Scheme 1 may be synthesized by a reaction path ofReaction Scheme 2 below, but it is not limited thereto.

Hal² is Br, Cl or I.

1. Synthesis Example of Sub 1-2

Sub 1-2a (50 g, 111.3 mmol), Sub 1-2b (25.2 g, 111.3 mmol), Pd₂(dba)₃(3.1 g, 3.3 mmol), P(t-Bu)₃ (1.4 g, 6.7 mmol), NaOt-Bu (21.4 g, 222.7mmol), and toluene (557 mL) in a round bottom flask were added, and thenthe reaction was carried out at 50° C. Upon completion of the reaction,the mixture was extracted with CH₂Cl₂ and water, the organic materiallayer was dried over MgSO₄, concentrated, and the resulting organicmaterial was recrystallized by silicagel column to obtain 45.1 g of aproduct. (Yield: 74%)

2. Synthesis Example of Sub 1-12

Sub 1-12a (50 g, 134.1 mmol), Sub 1-12b (52.6 g, 134.1 mmol), Pd₂(dba)₃(3.7 g, 4.0 mmol), P(t-Bu)₃ (1.6 g, 8.0 mmol), NaOt-Bu (25.8 g, 268.1mmol), and toluene (670 mL) in a round bottom flask were used in thesame manner as in Sub 1-2 to obtain 52.8 g of the product. (Yield: 72%)

In addition, compounds belonging to Sub 1 may be, but are not limitedto, the following compounds. Table 1 represents field desorption-massspectrometry (FD-MS) values of the compounds belonging to Sub 1.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 565.1 (C₃₆H₂₄BrNO =566.5) Sub 1-2 m/z = 546.04 (C₃₁H₁₉BrN₂OS = 547.47) Sub 1-3 m/z = 580.08(C₃₅H₂₁BrN₂O₂ = 581.47) Sub 1-4 m/z = 746.12 (C₄₇H₂₇BrN₂O₃ = 747.65) Sub1-5 m/z = 606.09 (C₃₇H₂₃BrN₂O₂ = 607.51) Sub 1-6 m/z = 663.06(C₃₈H₂₂BrN₃O₂S = 664.58) Sub 1-7 m/z = 641.14 (C₄₂H₂₈BrNO = 642.6) Sub1-8 m/z = 571.05 (C₃₂H₁₈BrN₃O₃ = 572.42) Sub 1-9 m/z = 491.06(C₂₈H₁₈BrN₃O = 492.38) Sub 1-10 m/z = 606.11 (C₃₆H₂₃BrN₄O = 607.51) Sub1-11 m/z = 530.06 (C₃₁H₁₉BrN₂O₂ = 531.41) Sub 1-12 m/z = 636.06(C₃₆H₂₁BrN₄OS = 637.56) Sub 1-13 m/z = 663.06 (C₃₈H₂₂BrN₃O₂S = 664.58)Sub 1-14 m/z = 720.14 (C₄₆H₂₉BrN₂O₂ = 721.65) Sub 1-15 m/z = 682.13(C₄₃H₂₇BrN₂O₂ = 683.61) Sub 1-16 m/z = 682.13 (C₄₃H₂₇BrN₂O₂ = 683.61)Sub 1-17 m/z = 539.09 (C₃₄H₂₂BrNO = 540.46) Sub 1-18 m/z = 580.08(C₃₅H₂₁BrN₂O₂ = 581.47) Sub 1-19 m/z = 696.09 (C₄₃H₂₅BrN₂OS = 697.65)Sub 1-20 m/z = 513.07 (C₃₂H₂₀BrNO = 514.42) Sub 1-21 m/z = 569.04(C₃₄H₂₀BrNOS = 570.5) Sub 1-22 m/z = 730.16 (C₄₈H₃₁BrN₂O = 731.69) Sub1-23 m/z = 751.15 (C₅₁H₃₀BrNO = 752.71) Sub 1-24 m/z = 686.07(C₄₁H₂₃BrN₂O₂S = 687.61) Sub 1-25 m/z = 672.09 (C₄₁H₂₅BrN₂OS = 673.63)Sub 1-26 m/z = 758.17 (C₄₈H₃₁BrN₄O = 759. 71) Sub 1-27 m/z = 680.11(C₄₃H₂₅BrN₂O₂ = 681.59) Sub 1-28 m/z = 755.16 (C₄₉H₃₀BrN₃O = 756.7) Sub1-29 m/z = 805.09 (C₄₈H₂₈BrN₃OS₂ = 806.8) Sub 1-30 m/z = 579.09(C₃₅H₂₂BrN₃O = 580.49) Sub 1-31 m/z = 732.14 (C₄₇H₂₉BrN₂O₂ = 733.67) Sub1-32 m/z = 687.07 (C₃₉H₂₂BrN₅OS = 688.6) Sub 1-33 m/z = 769.14(C₄₉H₂₈BrN₃O₂ = 770.69) Sub 1-34 m/z = 530.07 (C₃₀H₁₉BrN₄O = 531.41) Sub1-35 m/z = 663.06 (C₃₈H₂₂BrN₃O₂S = 664.58) Sub 1-36 m/z = 681.14(C₄₃H₂₈BrN₃O = 682.62) Sub 1-37 m/z = 720.14 (C₄₆H₂₉BrN₂O₂ = 721.65) Sub1-38 m/z = 646.14 (C₃₉H₂₇BrN₄O = 647.58) Sub 1-39 m/z = 786.13(C₅₀H₃₁BrN₂OS = 787.78) Sub 1-40 m/z = 873.31 (C₆₁H₃₉N₅O₂ = 874.02) Sub1-41 m/z = 545.06 (C₃₁H₂₀BrN₃S = 546.49) Sub 1-42 m/z = 696.09(C₄₃H₂₅BrN₂OS = 697.65) Sub 1-43 m/z = 562.02 (C₃₁H₁₉BrN₂S₂ = 563.53)Sub 1-44 m/z = 505.05 (C₃₀H₂₀BrNS = 506.46) Sub 1-45 m/z = 548.03(C₂₉H₁₇BrN₄OS = 549.45) Sub 1-46 m/z = 621.09 (C₃₇H₂₄BrN₃S = 622.58) Sub1-47 m/z = 427 (C₂₄H₁₄BrNS = 428. 35) Sub 1-48 m/z = 663.06(C₃₈H₂₂BrN₃O₂S = 664.58) Sub 1-49 m/z = 738.13 (C₄₆H₃₁BrN₂OS = 739.73)Sub 1-50 m/z = 713.08 (C₄₂H₂₄BrN₃O₂S = 714.64) Sub 1-51 m/z = 712.09(C₄₂H₂₅BrN₄OS = 713.65) Sub 1-52 m/z = 664.09 (C₃₈H₂₅BrN₄OS = 665.61)Sub 1-53 m/z = 900.18 (C₅₉H₃₇BrN₂OS = 901.92) Sub 1-54 m/z = 546.05(C₃₀H₁₉BrN₄S = 547. 47) Sub 1-55 m/z = 889.18 (C₅₇H₃₆BrN₃OS = 890.9) Sub1-56 m/z = 849.18 (C₅₅H₃₆BrN₃S = 850.88) Sub 1-57 m/z = 612.03(C₃₅H₂₁BrN₂S₂ = 613.59) Sub 1-58 m/z = 596.06 (C₃₅H₂₁BrN₂OS = 597.53)Sub 1-59 m/z = 652.03 (C₃₇H₂₁BrN₂OS₂ = 653.61) Sub 1-60 m/z = 570.04(C₃₃H₁₉BrN₂OS = 571.49) Sub 1-61 m/z = 646.07 (C₃₉H₂₃BrN₂OS = 647.59)Sub 1-62 m/z = 745.03 (C₄₂H₂₄BrN₃S₃ = 746.76) Sub 1-63 m/z = 546.04(C₃₁H₁₉BrN₂OS = 547.47) Sub 1-64 m/z = 595.07 (C₃₅H₂₂BrN₃S = 596.55) Sub1-65 m/z = 707.13 (C₄₆H₃₀BrNS = 708.72) Sub 1-66 m/z = 646.07(C₃₉H₂₃BrN₂OS = 647.59) Sub 1-67 m/z = 546.04 (C₃₁H₁₉BrN₂OS = 547.47)Sub 1-68 m/z = 646.08 (C₃₈H₂₃BrN₄S = 647.59) Sub 1-69 m/z = 789.11(C₄₈H₂₈BrN₃O₂S = 790.74) Sub 1-70 m/z = 829.1 (C₅₀H₂₈BrN₃O₃S = 830.76)Sub 1-71 m/z = 638.05 (C₃₇H₂₃BrN₂S₂ = 639.63) Sub 1-72 m/z = 814.18(C₅₁H₃₅BrN₄S = 815.83) Sub 1-73 m/z = 698.1 (C₄₃H₂₇BrN₂OS = 699.67) Sub1-74 m/z = 714.08 (C₄₃H₂₇BrN₂S₂ = 715.73) Sub 1-75 m/z = 620.06(C₃₇H₂₁BrN₂OS = 621.55) Sub 1-76 m/z = 545.06 (C₃₁H₂₀BrN₃S = 546.49) Sub1-77 m/z = 712.08 (C₄₃H₂₅BrN₂O₂S = 713.65) Sub 1-78 m/z = 646.07(C₃₉H₂₃BrN₂OS = 647.59) Sub 1-79 m/z = 820.07 (C₄₉H₂₉BrN₂S₃ = 821.87)Sub 1-80 m/z = 788.11 (C₄₉H₂₉BrN₂O₂S = 789.75) Sub 1-81 m/z = 645.09(C₃₉H₂₄BrN₃S = 646.61) Sub 1-82 m/z = 713.11 (C₄₃H₂₈BrN₃OS = 714.68) Sub1-83 m/z = 713.11 (C₄₃H₂₈BrN₃OS = 714.68) Sub 1-84 m/z = 865.18(C₅₅H₃₆BrN₃OS = 866.88) Sub 1-85 m/z = 494.10 (C₃₀H₁₅D₅BrNO = 495.43)Sub 1-86 m/z = 564.03 (C₃₁H₁₈BrFN₂OS = 565.46) Sub 1-87 m/z = 644.10(C₃₇H₂₉BrN₂S₂ = 645.68) Sub 1-88 m/z = 611.09 (C₃₇H₂₆BrNOS = 612.59)

II. Synthesis of Sub 2

Sub 2 of the Reaction Scheme 1 may be synthesized according to, but notlimited to, Reaction Scheme 3 below.

1. Synthesis Example of Sub 2-2

Sub 2-2a (50 g, 253.8 mmol), Sub 2-1b (23.6 g, 253.8 mmol), Pd₂(dba)₃(7.0 g, 7.6 mmol), P(t-Bu)₃ (3.1 g, 15.2 mmol), NaOt-Bu (48.8 g, 507.5mmol), and toluene (1269 mL) in a round bottom flask were added, andthen the reaction was carried out at 80° C. After completion of thereaction, the reaction was extracted with CH₂Cl₂ and water, the organicmaterial layer was dried over MgSO₄, concentrated, and the resultingorganic material was recrystallized using silicagel column to obtain29.0 g of a product. (Yield: 76%)

2. Synthesis Example of Sub 2-8

Sub 2-8a (50 g, 182.4 mmol), Sub 2-1b (17.0 g, 182.4 mmol), Pd₂(dba)₃(5.0 g, 5.5 mmol), P(t-Bu)₃ (2.2 g, 10.9 mmol), NaOt-Bu (35.1 g, 364.8mmol), and toluene (912 mL) in a round bottom flask were used in thesame manner as in Sub 2-2 to obtain 38.6 g of the product. (Yield: 74%)

3. Synthesis Example of Sub 2-44

Sub 2-8a (50 g, 182.4 mmol), Sub 2-2b (33.4 g, 182.4 mmol), Pd₂(dba)₃(5.0 g, 5.5 mmol), P(t-Bu)₃ (2.2 g, 10.9 mmol), NaOt-Bu (35.1 g, 346.8mmol), and toluene (912 mL) in a round bottom flask were used in thesame manner as in Sub 2-2 to obtain 48.1 g of the product. (Yield: 70%)

Compounds belonging to Sub 2 may be, but are not limited to, thefollowing compounds. Table 2 represents FD-MS values of the compoundsbelonging to Sub 2.

TABLE 2 Compound FD-MS Compound FD-MS Sub 2-1 m/z = 210.08 (C₁₃H₁₀N₂O =210.24) Sub 2-2 m/z = 169.09 (C₁₂H₁₁N = 169.23) Sub 2-3 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-4 m/z = 403.13 (C₂₆H₁₇N₃O₂ = 403.44) Sub 2-5m/z = 251.07 (C₁₄H₉N₃O₂ = 251.25) Sub 2-6 m/z = 285.13 (C₁₉H₁₅N₃ =285.35) Sub 2-7 m/z = 403.13 (C₂₆H₁₇N₃O₂ = 403.44) Sub 2-8 m/z = 286.11(C₁₉H₁₄N₂O = 286.33) Sub 2-9 m/z = 286.11 (C₁₉H₁₄N₂O = 286.33) Sub 2-10m/z = 226.06 (C₁₃H₁₀N₂S = 226.3) Sub 2-11 m/z = 335.14 (C₂₃H₁₇N₃ =335.41) Sub 2-12 m/z = 526.2 (C₃₈H₂₆N₂O = 526.64) Sub 2-13 m/z = 260.09(C₁₇H₁₂N₂O = 260.3) Sub 2-14 m/z = 286.12 (C₁₈H₁₄N₄ = 286.34) Sub 2-15m/z = 392.1 (C₂₅H₁₆N₂OS = 392.48) Sub 2-16 m/z = 219.1 (C₁₆H₁₃N =219.29) Sub 2-17 m/z = 362.14 (C₂₅H₁₈N₂O = 362.43) Sub 2-18 m/z = 416.13(C₂₆H₁₆N₄O₂ = 416.44) Sub 2-19 m/z = 284.09 (C₁₉H₁₂N₂O = 284.32) Sub2-20 m/z = 285.13 (C₁₉H₁₅N₃ = 285.35) Sub 2-21 m/z = 284.09 (C₁₉H₁₂N₂O =284.32) Sub 2-22 m/z = 286.12 (C₁₈H₁₄N₄ = 286.34) Sub 2-23 m/z = 209.1(C₁₃H₁₁N₃ = 209.25) Sub 2-24 m/z = 362.15 (C₂₄H₁₈N₄ = 362.44) Sub 2-25m/z = 302.09 (C₁₉H₁₄N₂S = 302.4) Sub 2-26 m/z = 211.07 (C₁₂H₉N₃O =211.22) Sub 2-27 m/z = 361.16 (C₂₅H₁₉N₃ = 361.45) Sub 2-28 m/z = 286.11(C₁₉H₁₄N₂O = 286.33) Sub 2-29 m/z = 403.13 (C₂₆H₁₇N₃O₂ = 403.44) Sub2-30 m/z = 620.2 (C₄₂H₂₈N₄S = 620.77) Sub 2-31 m/z = 250.09 (C₁₄H₁₀N₄O =250.26) Sub 2-32 m/z = 412.16 (C₂₉H₂₀N₂O = 412.49) Sub 2-33 m/z = 285.13(C₁₉H₁₅N₃ = 285.35) Sub 2-34 m/z = 167.07 (C₁₂H₉N = 167.21) Sub 2-35 m/z= 437.19 (C₃₁H₂₃N₃ = 437.55) Sub 2-36 m/z = 302.09 (C₁₉H₁₄N₂S = 302.4)Sub 2-37 m/z = 392.1 (C₂₅H₁₆N₂OS = 392.48) Sub 2-38 m/z = 286.11(C₁₉H₁₄N₂O = 286.33) Sub 2-39 m/z = 286.12 (C₁₈H₁₄N₄ = 286.34) Sub 2-40m/z = 362.15 (C₂₄H₁₈N₄ = 362.44) Sub 2-41 m/z = 403.13 (C₂₆H₁₇N₃O₂ =403.44) Sub 2-42 m/z = 401.16 (C₂₆H₁₉N₅ = 401.47) Sub 2-43 m/z = 284.09(C₁₉H₁₂N₂O = 284.32) Sub 2-44 m/z = 376.12 (C₂₅H₁₆N₂O₂ = 376.42)

III. Synthesis Examples of Final Products 1. Synthesis Example of P-2

Sub 1-2 (45.1 g, 82.4 mmol), Sub 2-2 (13.9 g, 82.4 mmol), Pd₂(dba)₃ (2.3g, 2.5 mmol), P(t-Bu)₃ (1.0 g, 4.9 mmol), NaOt-Bu (15.8 g, 164.8 mmol),and toluene (412 mL) in a round bottom flask were used in the samemanner as in Sub 2-2 to obtain 35.6 g of the product. (Yield: 68%)

2. Synthesis Example of P-12

Sub 1-12 (52.8 g, 84.7 mmol), Sub 2-2 (14.3 g, 84.7 mmol), Pd₂(dba)₃(2.3 g, 2.5 mmol), P(t-Bu)₃ (1.0 g, 5.1 mmol), NaOt-Bu (16.3 g, 169.3mmol), and toluene (423 mL) in a round bottom flask were used in thesame manner as in Sub 2-2 to obtain 47.3 g of the product. (Yield: 77%)

3. Synthesis Example of P-41

Sub 1-41 (50.0 g, 101.2 mmol), Sub 2-23 (42.3 g, 202.3 mmol), Pd₂(dba)₃(2.8 g, 3.0 mmol), P(t-Bu)₃ (1.2 g, 6.1 mmol), NaOt-Bu (19.4 g, 202.3mmol), and toluene (506 mL) in a round-bottom flask were used in thesame manner as in Sub 2-2 to obtain 53.9 g of the product. (Yield: 71%)

4. Synthesis Example of P-63

Sub 1-63a (50.0 g, 146.2 mmol), Sub 2-8 (83.7 g, 292.4 mmol), Pd₂(dba)₃(4.0 g, 4.4 mmol), P(t-Bu)₃ (1.8 g, 8.8 mmol), NaOt-Bu (28.1 g, 292.4mmol), and toluene (731 mL) in a round-bottom flask were used in thesame manner as in Sub 2-2 to obtain 86.9 g of a product. (Yield: 79%)

5. Synthesis Example of P-67

Sub 1-67a (50.0 g, 146.2 mmol), Sub 2-8 (83.7 g, 292.4 mmol), Pd₂(dba)₃(4.0 g, 4.4 mmol), P(t-Bu)₃ (1.8 g, 8.8 mmol), NaOt-Bu (28.1 g, 292.4mmol), and toluene (731 mL) in a round bottom flask were used in thesame manner as in Sub 2-2, to obtain 88.0 g of a product. (Yield: 80%)

In addition, the FD-MS values of the compounds P-1 to P-88 according tothe present disclosure fabricated according to the above-describedsynthesis examples are represented in Table 3.

TABLE 3 Compound FD-MS Compound FD-MS P-1 m/z = 695.26 (C₄₉H₃₃N₃O₂ =695.82) P-2 m/z = 635.2 (C₄₃H₂₉N₃OS = 635 79) P-3 m/z = 669.24(C₄₇H₃₁N₃O₂ = 669.78) P-4 m/z = 876.27 (C₆₀H₃₆N₄O₄ = 876.97) P-5 m/z =736.25 (C₅₀H₃₂N₄O₃ = 736.83) P-6 m/z = 858.21 (C₅₆H₃₄N₄O₂S₂ = 859.03)P-7 m/z = 964.34 (C₆₈H₄₄N₄O₃ = 965.13) P-8 m/z = 742.2 (C₄₆H₂₆N₆O₅ =742.75) P-9 m/z = 696.26 (C₄₇H₃₂N₆O = 696.81) P-10 m/z = 929.31(C₆₂H₃₉N₇O₃ = 930. 04) P-11 m/z = 736.25 (C₅₀H₃₂N₄O₃ = 736.83) P-12 m/z= 725.22 (C₄₈H₃₁N₅OS = 725.87) P-13 m/z = 752.22 (C₅₀H₃₂N₄O₂S = 752.89)P-14 m/z = 809.3 (C₅₈H₃₉N₃O₂ = 809.97) P-15 m/z = 771.29 (C₅₅H₃₇N₃O₂ =771.92) P-16 m/z = 888.31 (C₆₂H₄₀N₄O₃ = 889.03) P-17 m/z = 685.22(C₄₇H₃₁N₃OS = 685.85) P-18 m/z = 786.26 (C₅₄H₃₄N₄O₃ = 786.89) P-19 m/z =951.3 (C₆₆H₄₁N₅OS = 952.15) P-20 m/z = 959.35 (C₇₀H₄₅N₃O₂ = 960.15) P-21m/z = 749.21 (C₅₁H₃₁N₃O₂S = 749.89) P-22 m/z = 936.35 (C₆₇H₄₄N₄O₂ =937.12) P-23 m/z = 957.35 (C₆₉H₄₃N₅O = 958.14) P-24 m/z = 998.24(C₆₆H₃₈N₄O₃S₂ = 999.18) P-25 m/z = 761.25 (C₅₃H₃₅N₃OS = 761.94) P-26 m/z= 847.33 (C₆₀H₄₁N₅O = 848.02) P-27 m/z = 819.29 (C₅₉H₃₇N₃O₂ = 819.96)P-28 m/z = 844.32 (C₆₁H₄₀N₄O = 845.02) P-29 m/z = 894.25 (C₆₀H₃₈N₄OS₂ =895.11) P-30 m/z = 668.26 (C₄₇H₃₂N₄O = 668.8) P-31 m/z = 1014.36(C₇₂H₄₆N₄O₃ = 1015.19) P-32 m/z = 1023.27 (C₆₅H₃₇N₉O₃S = 1024.13) P-33m/z = 973.31 (C₆₈H₃₉N₅O₃ = 974.09) P-34 m/z = 736.27 (C₄₈H₃₂N₈O =736.84) P-35 m/z = 869.25 (C₅₇H₃₅N₅O₃S = 870) P-36 m/z = 886.34(C₆₂H₄₂N₆O = 887.06) P-37 m/z = 924.31 (C₆₅H₄₀N₄O₃ = 925.06) P-38 m/z =968.4 (C₆₆H₄₈N₈O = 969.17) P-39 m/z = 992.32 (C₆₉H₄₄N₄O₂S = 993.2) P-40m/z = 1143.4 (C₇₈H₄₉N₉O₂ = 1144.31) P-41 m/z = 750.26 (C₅₀H₃₄N₆S =750.92) P-42 m/z = 785.25 (C₅₅H₃₅N₃OS = 785.97) P-43 m/z = 784.18(C₅₀H₃₂N₄S₃ = 785.01) P-44 m/z = 787.28 (C₅₄H₃₇N₅S = 787. 99) P-45 m/z =679.18 (C₄₁H₂₅N₇O₂S = 679.76) P-46 m/z = 902.32 (C₆₂H₄₂N₆S = 903.12)P-47 m/z = 633.19 (C₄₃H₂₇N₃OS = 633.77) P-48 m/z = 986.27 (C₆₄H₃₈N₆O₄S =987.11) P-49 m/z = 827.3 (C₅₈H₄₁N₃OS = 828.05) P-50 m/z = 802.24(C₅₄H₃₄N₄O₂S = 802.95) P-51 m/z = 1252.37 (C₈₄H₅₂N₈OS₂ = 1253.52) P-52m/z = 834.25 (C₅₂H₃₄N₈O₂S = 834.96) P-53 m/z = 1232.41 (C₈₈H₅₆N₄O₂S =1233.5) P-54 m/z = 751.25 (C₄₉H₃₃N₇S = 751.91) P-55 m/z = 976.32(C₆₉H₄₄N₄OS = 977.2) P-56 m/z = 1206.44 (C₈₆H₅₈N₆S = 1207.51) P-57 m/z =834.19 (C₅₄H₃₄N₄S₃ = 835.07) P-58 m/z = 685.22 (C₄₇H₃₁N₃OS = 685.85)P-59 m/z = 964.2 (C₆₂H₃₆N₄O₂S₃ = 965.18) P-60 m/z = 776.22 (C₅₂H₃₂N₄O₂S= 776.91) P-61 m/z = 852.26 (C₅₈H₃₆N₄O₂S = 853.01) P-62 m/z = 951.22(C₆₁H₃₇N₅OS₃ = 952.18) P-63 m/z = 752.22 (C₅₀H₃₂N₄O₂S = 752.89) P-64 m/z= 800.27 (C₅₄H₃₆N₆S = 800.98) P-65 m/z = 913.32 (C₆₄H₄₃N₅S = 914.14)P-66 m/z = 735.23 (C₅₁H₃₃N₃OS = 735.91) P-67 m/z = 752.22 (C₅₀H₃₂N₄O₂S =752.89) P-68 m/z = 928.31 (C₆₂H₄₀N₈S = 929.12) P-69 m/z = 878.27(C₆₀H₃₈N₄O₂S = 879.05) P-70 m/z = 1152.31 (C₇₆H₄₄N₆O₅S = 1153.29) P-71m/z = 727.21 (C₄₉H₃₃N₃S₂ = 727.94) P-72 m/z = 1135.41 (C₇₇H₅₃N₉S =1136.39) P-73 m/z = 904.29 (C₆₂H₄₀N₄O₂S = 905.09) P-74 m/z = 936.24(C₆₂H₄₀N₄S₃ = 937.21) P-75 m/z = 824.22 (C₅₆H₃₂N₄O₂S = 824.96) P-76 m/z= 632.2 (C₄₃H₂₈N₄S = 632.79) P-77 m/z = 917.28 (C₆₂H₃₉N₅O₂S = 918.09)P-78 m/z = 852.26 (C₅₈H₃₆N₄O₂S = 853.01) P-79 m/z = 1026.25 (C₆₈H₄₂N₄OS₃= 1027.29) P-80 m/z = 1084.31 (C₇₄H₄₄N₄O₄S = 1085.25) P-81 m/z = 851.27(C₅₈H₃₇N₅OS = 852.03) P-82 m/z = 919.30 (C₆₂H₄₁N₅O₂S = 920.10) P-83 m/z= 935.28 (C₆₂H₄₁N₅OS₂ = 936.16) P-84 m/z = 1071.36 (C₇₄H₄₉N₅O₂S =1072.30) P-85 m/z = 716.27 (C₄₉H₂₈D₅N3OS = 716.91) P-86 m/z = 770.22(C₅₀H₃₁FN₄O₂S = 770.22) P-87 m/z = 850.28 (C₅₆H₄₂N₄OS₂ = 851.10) P-88m/z = 817.28 (C₅₆H₃₉N₃O₂S = 818.01)

Evaluation of the Fabrication of Organic Electric Element

Embodiment 1) Evaluation of the Fabrication of Blue Organic ElectricElement [Example 1] to [Example 20] Blue Organic Light Emitting Element(Capping Layer)

An organic light emitting element was fabricated by a common methodusing a compound of the present disclosure as an auxiliary emittinglayer. First, a hole injection layer was formed by vacuum-depositing4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter,referred to as “2-TNATA”) to a thickness of 60 nm on an indium tin oxide(ITO) layer (i.e. a positively charged electrode) formed on a glasssubstrate, and then a hole transport layer was formed byvacuum-depositingN,N′-bis(l-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter, referred to as “NPB”) to a thickness of 60 nm on the holeinjection layer. Subsequently, an emitting layer was formed byvacuum-depositing a host material to a thickness of 30 nm on the holetransport layer, the host material being9,10-di(naphthalen-2-yl)anthracene doped with a dopant material BD-052X(Idemitsu kosan) at a weight ratio of 93:7. Afterwards, a hole blockinglayer was formed by vacuum-depositing(1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, referred to as “BAlq”) to a thickness of 10 nm on theemitting layer, and then an electron transport layer was formed byvacuum-depositing tris(8-quinolinolato)aluminum (hereinafter, referredto as “Alq3”) and Bis(10-hydroxybenzo[h]quinolinato)beryllium(hereinafter, referred to as “BeBq₂”) mixed in a 1:1 ratio to athickness of 45 nm on the hole blocking layer. Thereafter, an electroninjection layer was formed by depositing an alkali-metal halide LiF to athickness of 0.2 nm, and then a negatively charged electrode was formedby depositing Al to a thickness of 150 nm. Consequently, the organiclight emitting element was fabricated by forming a capping layer with athickness of 60 nm on the compounds of the present disclosurerepresented by the Formula 1 as shown in Table 4.

Comparative Example 1

An organic light emitting elements was fabricated in the same manner asin the Example 1 except for not using the capping layer.

Comparative Examples 2 to 5

Organic light emitting elements were fabricated in the same manner as inthe Example 1 except that Comparative Compounds 1 to 4 below were usedas the capping layer material in place of the compounds according to thepresent disclosure represented by the Formula 1.

The electroluminescence (EL) properties of the organic light emittingelements, fabricated according to Examples 1 to 20 according to thepresent disclosure and the Comparative Examples 1 to 5, were measuredusing PR-650 available from Photo Research by applying a forward-bias DCvoltage to the organic light emitting elements. The T95 lifetimes of theorganic light emitting elements fabricated were measured at a referenceluminance of 500 cd/m² using lifetime measuring equipment fabricated byMcScience. The results of the measurement are illustrated in Table 4below.

TABLE 4 Driving Current Voltage Density Brightness Efficiency LifetimeCIE Compound (V) (mA/cm²) (cd/m²) (cd/A) T95 (hr) x y Comparative — 6.522.7 500 2.2 60.3 0.15 0.15 Example 1 Comparative Comparative 6.4 20.0500 2.5 61.8 0.15 0.10 Example 2 Compound 1 Comparative Comparative 6.516.1 500 3.1 62.3 0.14 0.09 Example 3 Compound 2 Comparative Comparative6.5 15.6 500 3.2 63.1 0.15 0.09 Example 4 Compound 3 ComparativeComparative 6.4 14.7 500 3.4 63.7 0.15 0.08 Example 5 Compound 4 Example1 P-2 6.5 11.4 500 4.4 62.7 0.14 0.07 Example 2 P-11 6.4 10.7 500 4.763.0 0.14 0.07 Example 3 P-12 6.5 11.3 500 4.4 62.9 0.14 0.07 Example 4P-13 6.4 10.9 500 4.6 63.4 0.14 0.07 Example 5 P-16 6.4 11.2 500 4.562.9 0.14 0.07 Example 6 P-22 6.5 11.4 500 4.4 62.2 0.14 0.07 Example 7P-24 6.4 11.2 500 4.5 63.8 0.14 0.07 Example 8 P-26 6.4 10.7 500 4.762.6 0.14 0.07 Example 9 P-34 6.5 11.0 500 4.5 63.8 0.14 0.07 Example 10P-36 6.4 10.9 500 4.6 62.6 0.14 0.07 Example 11 P-41 6.4 10.7 500 4.762.1 0.14 0.07 Example 12 P-42 6.4 10.8 500 4.6 63.9 0.14 0.07 Example13 P-43 6.4 10.7 500 4.7 63.6 0.14 0.07 Example 14 P-44 6.5 11.6 500 4.364.0 0.14 0.07 Example 15 P-45 6.4 11.6 500 4.3 63.6 0.14 0.07 Example16 P-60 6.4 11.5 500 4.3 63.3 0.14 0.07 Example 17 P-63 6.4 10.4 500 4.863.1 0.14 0.07 Example 18 P-66 6.4 11.5 500 4.4 63.5 0.14 0.07 Example19 P-67 6.4 10.2 500 4.9 63.9 0.14 0.07 Example 20 P-76 6.4 11.5 500 4.363.2 0.14 0.07

Embodiment 2) Evaluation of the Fabrication of Green Organic ElectricElement [Example 21] to [Example 40] Green Organic Light EmittingElement (Capping Layer)

Organic light emitting elements were fabricated in the same manner as inthe Example 1 except that CBP[4,4′-N,N′-dicarbazole-biphenyl] instead of9,10-di(naphthalen-2-yl)anthracene as a host, andtris(2-phenylpyridine)-iridium instead of BD-052X (Idemitsu kosan) as adopant was used in a weight ratio of 95:5.

Comparative Example 6

An organic light emitting elements was fabricated in the same manner asin the Example 21 except for not using the capping layer.

Comparative Examples 7 to 10

Organic light emitting elements were fabricated in the same manner as inthe Example 21 except that the Comparative Compounds 1 to 4 were used asthe capping layer material in place of the compounds according to thepresent disclosure represented by the Formula 1.

The electroluminescence (EL) properties of the organic light emittingelements, fabricated according to Examples 21 to 40 according to thepresent disclosure and the Comparative Examples 6 to 10, were measuredusing PR-650 available from Photo Research by applying a forward-bias DCvoltage to the organic light emitting elements. The T95 lifetimes of theorganic light emitting elements fabricated were measured at a referenceluminance of 5000 cd/m² using lifetime measuring equipment fabricated byMcScience. The results of the measurement are illustrated in Table 5below.

TABLE 5 Driving Current Voltage Density Brightness Efficiency LifetimeCIE Compound (V) (mA/cm²) (cd/m²) (cd/A) T95 (hr) x y Comparative — 6.423.1 5000 21.6 69.6 0.34 0.61 Example 6 Comparative Comparative 6.3 17.45000 28.8 70.2 0.35 0.62 Example 7 Compound 1 Comparative Comparative6.3 15.5 5000 32.3 70.2 0.34 0.68 Example 8 Compound 2 ComparativeComparative 6.4 14.5 5000 34.4 70.1 0.35 0.67 Example 9 Compound 3Comparative Comparative 6.4 14.4 5000 34.7 70.3 0.36 0.66 Example 10Compound 4 Example 21 P-2 6.3 11.6 5000 43.1 70.8 0.33 0.65 Example 22P-11 6.4 10.9 5000 45.9 70.1 0.33 0.65 Example 23 P-12 6.3 11.5 500043.3 70.9 0.33 0.65 Example 24 P-13 6.4 11.1 5000 44.9 70.8 0.33 0.65Example 25 P-16 6.3 11.4 5000 44.0 70.4 0.33 0.64 Example 26 P-22 6.411.5 5000 43.5 70.3 0.33 0.65 Example 27 P-24 6.4 11.3 5000 44.3 70.50.33 0.64 Example 28 P-26 6.3 10.8 5000 46.4 70.4 0.33 0.64 Example 29P-34 6.3 11.3 5000 44.4 70.7 0.33 0.65 Example 30 P-36 6.3 11.1 500045.2 70.9 0.33 0.65 Example 31 P-41 6.3 10.9 5000 46.0 70.2 0.33 0.64Example 32 P-42 6.3 10.9 5000 45.7 70.8 0.33 0.64 Example 33 P-43 6.310.7 5000 46.6 70.0 0.33 0.64 Example 34 P-44 6.4 11.9 5000 42.1 70.70.33 0.64 Example 35 P-45 6.3 11.8 5000 42.4 70.8 0.33 0.65 Example 36P-60 6.4 11.8 5000 42.5 70.6 0.33 0.64 Example 37 P-63 6.4 10.5 500047.6 70.1 0.33 0.65 Example 38 P-66 6.4 11.4 5000 43.7 70.9 0.33 0.64Example 39 P-67 6.4 10.5 5000 47.6 70.1 0.33 0.65 Example 40 P-76 6.311.7 5000 42.6 70.5 0.33 0.64

Embodiment 3) Evaluation of the Fabrication of Red Organic ElectricElement [Example 41] to [Example 60] Red Organic Light Emitting Element(Capping Layer)

Organic light emitting elements were fabricated in the same manner as inthe Example 1 except that CBP[4,4′-N,N′-dicarbazole-biphenyl] instead of9,10-di(naphthalen-2-yl)anthracene as a host, and (piq)₂Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] instead ofBD-052X (Idemitsu kosan) as a dopant was used in a weight ratio of 95:5.

Comparative Example 11

An organic light emitting elements was fabricated in the same manner asin the Example 41 except for not using the capping layer.

Comparative Examples 12 to 15

Organic light emitting elements were fabricated in the same manner as inthe Example 41 except that the Comparative Compounds 1 to 4 were used asthe capping layer material in place of the compounds according to thepresent disclosure represented by the Formula 1.

The electroluminescence (EL) properties of the organic light emittingelements, fabricated according to Examples 41 to 60 according to thepresent disclosure and the Comparative Examples 11 to 15, were measuredusing PR-650 available from Photo Research by applying a forward-bias DCvoltage to the organic light emitting elements. The T95 lifetimes of theorganic light emitting elements fabricated were measured at a referenceluminance of 2500 cd/m² using lifetime measuring equipment fabricated byMcScience. The results of the measurement are illustrated in Table 6below.

TABLE 6 Driving Current Voltage Density Brightness Efficiency LifetimeCIE Compound (V) (mA/cm²) (cd/m²) (cd/A) T95 (hr) x y Comparative — 6.632.9 2500 7.6 57.2 0.62 0.39 Example 11 Comparative Comparative 6.5 30.92500 8.1 58.0 0.63 0.32 Example 12 Compound 1 Comparative Comparative6.6 26.9 2500 9.3 62.4 0.64 0.34 Example 13 Compound 2 ComparativeComparative 6.6 26.9 2500 9.3 62.1 0.63 0.39 Example 14 Compound 3Comparative Comparative 6.5 26.6 2500 9.4 62.2 0.63 0.38 Example 15Compound 4 Example 41 P-2 6.5 20.5 2500 12.2 62.2 0.67 0.34 Example 42P-11 6.5 18.1 2500 13.8 63.6 0.67 0.34 Example 43 P-12 6.6 20.0 250012.5 63.1 0.67 0.34 Example 44 P-13 6.5 18.2 2500 13.7 63.7 0.67 0.34Example 45 P-16 6.6 19.1 2500 13.1 62.4 0.67 0.34 Example 46 P-22 6.619.5 2500 12.8 62.2 0.67 0.34 Example 47 P-24 6.5 18.8 2500 13.3 62.10.67 0.34 Example 48 P-26 6.5 17.9 2500 14.0 62.8 0.67 0.34 Example 49P-34 6.5 18.4 2500 13.6 63.9 0.67 0.34 Example 50 P-36 6.5 18.0 250013.9 62.2 0.67 0.34 Example 51 P-41 6.5 17.7 2500 14.1 62.5 0.67 0.34Example 52 P-42 6.5 17.9 2500 14.0 62.8 0.67 0.34 Example 53 P-43 6.518.4 2500 13.6 63.4 0.67 0.34 Example 54 P-44 6.6 21.9 2500 11.4 62.60.67 0.34 Example 55 P-45 6.5 21.4 2500 11.7 61.1 0.67 0.34 Example 56P-60 6.5 21.0 2500 11.9 62.4 0.67 0.34 Example 57 P-63 6.5 17.6 250014.2 62.9 0.67 0.34 Example 58 P-66 6.5 19.2 2500 13.0 62.5 0.67 0.34Example 59 P-67 6.6 17.2 2500 14.5 62.8 0.67 0.34 Example 60 P-76 6.520.7 2500 12.1 63.5 0.67 0.35

As seen from the results of Tables 4 to 6, it may be seen that, when theorganic light-emitting elements were fabricated using the organic lightemitting element material according to the present disclosure as thecapping layer material represented by the Formula 1, the organic lightemitting elements may have a high purity and improved luminousefficiency compared to the comparative examples. It may be seen that thecolor purity and luminous efficiency are increased by the introductionof the capping layer, comparing the results according to the presence orabsence of the capping layer. It may be seen that when the compoundaccording to the present disclosure is applied rather than thecomparative compounds 1 to 4 as the capping layer, the luminousefficiency is significantly improved.

When the capping layer is introduced, the SPPs (Surface plasmonpolaritons) are generated at the interface between the Al electrode andthe high refractive organic material. In this case, the TE (transverseelectric) polarized light is annihilated on the capping layer surface inthe vertical direction by an evanescent wave and TM polarized lightmoving along the cathode and the capping layer is amplified by surfaceplasma resonance, thereby enabling high efficiency and effective colorpurity control.

As described above, in the visible light wavelength band of 430 nm to780 nm, the compound according to the present disclosure includes, as acore, a substituent group in which a benzene ring such as benzoimidazoleor benzoxazole and the five-membered ring with at least one N is fusedin order to increase the refractive index and dibenzothiophene ordibenzofuran including sulfur or oxygen atom, which is a hetero elementwith a high refractive index, and thus has a higher refractive indexthan that of the comparative compound B or the comparative compound Cand thus, the light generated in the organic material layer increasesthe efficiency of extraction to the outside of the organic lightemitting element by the principle of constructive interference, therebygreatly contributing to the improvement of the light efficiency of theorganic electric element.

The above description provides examples of the present disclosure forillustrative purposes only. Those having ordinary knowledge in thetechnical field, to which the present disclosure pertains, willappreciate that various modifications are possible without departingfrom the essential features of the present disclosure. Therefore, theexamples disclosed in the present disclosure are intended to illustratethe technical idea of the present disclosure, and the scope of thepresent disclosure is not limited by the examples.

The scope of the present disclosure shall be construed on the basis ofthe accompanying claims in such a manner that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentdisclosure.

DESCRIPTION OF SYMBOLS

-   -   100, 200, 300: organic electric element    -   110, 110, 310: first electrode    -   20, 220, 320: hole injection layer    -   321: first hole injection layer    -   130, 230: hole transport layer    -   331: first hole transport layer    -   332: second hole transport layer    -   243: buffer layer    -   253: light emitting auxiliary layer    -   140, 240: light emitting layer    -   341: first light emitting layer    -   342: second emitting layer    -   150, 250: electron transport layer    -   351: first electron transport layer    -   352: second electron transport layer    -   160, 260, 360: electron injection layer    -   170, 270, 370: second electrode    -   180, 280, 380: capping layer    -   390: first charge generating layer    -   391: second charge generating layer    -   ST1: first stack    -   ST2: second stack    -   CGL: charge generating layer

1. An organic electric element comprising: a first electrode; a secondelectrode; an organic material layer located between the first electrodeand the second electrode, and a capping layer disposed on at least oneof one surface of the first electrode opposite to the organic materiallayer and one surface of the second electrode opposite to the organicmaterial layer, wherein the capping layer comprises a compoundrepresented by following Formula 1-T:

in the Formula 1-T, 1) Ar¹ to Ar⁴ are each independently selected from agroup consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀hetero ring group comprising at least one heteroatom selected from amongO, N, S, Si, or P; and a fused ring group of a C₃-C₆₀ aliphatic ring anda C₆-C₆₀ aromatic ring, 2) At least one of Ar¹ to Ar⁴ is represented byformula 1-1, 3) L¹ and L² are each independently selected from a groupconsisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylenegroup; a C₂-C₆₀ hetero ring group comprising at least one heteroatomselected from among O, N, S, Si, or P; and a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, 4) L³ to L⁶ are eachindependently selected from a group consisting of a single bond; aC₆-C₆₀ arylene group; a fluorenylene group; a C₂-C₆₀ hetero ring groupcomprising at least one heteroatom selected from among O, N, S, Si, orP; and a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic, 5) R¹ and R² are each independently selected from the groupconsisting of deuterium; a C₆-C₆₀ aryl group; a fluorenyl group; aC₂-C₆₀ hetero ring group comprising at least one heteroatom selectedfrom among O, N, S, Si, or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; and -L′-N(R_(a))(R_(b)), and one ormore adjacent R¹s are the same or different and the adjacent R¹s may bebonded to each other to form a ring, and one or more adjacent R²s arethe same or different and the adjacent R²s may be bonded to each otherto form a ring, 6) R³ is each independently selected from the groupconsisting of deuterium; a C₆-C₆₀ aryl group; a fluorenyl group; aC₂-C₆₀ hetero ring group comprising at least one heteroatom selectedfrom among O, N, S, Si, or P; and a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; and -L′-N(R_(a))(R_(b)), andone or more adjacent R³s are the same or different and the adjacent R³smay be bonded to each other to form a ring, 7) a and b are eachindependently an integer of 0 to 3, c is an integer of 0 to 4, and whentwo or more of Ar¹ to Ar⁴ are represented by the formula 1-1, aplurality of c's are the same or may be different, 8) L′ is eachindependently selected from a group consisting of a single bond; C₆-C₆₀arylene group; fluorenylene group; a C₂-C₆₀ hetero ring group comprisingat least one heteroatom selected from among O, N, S, Si, or P; and afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring,9) R_(a) and R_(b) are each independently selected from a groupconsisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heteroring group comprising at least one heteroatom selected from among O, N,S, Si, or P; and a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring, 10) X is O or S, 11) Ring A is each independentlyselected from the group consisting of benzene, naphthalene, phenanthreneand anthracene, 12) Y is each independently CR^(a)R^(b) or NR^(c), andwhen Y is bonded to the formula 1-T, it may be N or C; 13) Y′ is eachindependently N, O or S, 14) R^(a), R^(b) and R^(c) are eachindependently hydrogen; deuterium; a C₆-C₆₀ aryl group; a fluorenylgroup; a C₂-C₆₀ hetero ring group comprising at least one heteroatomselected from among O, N, S, Si, or P; and a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, 15) adjacent L¹ andR¹, L¹ and Ar¹, L¹ and Ar², L¹ and L³, and L⁴, adjacent L² and R², L²and Ara, L² and Ar⁴, L² and L⁵, L² and L⁶ may be bonded to form a ring,16) in Ar¹ to Ar⁴, L¹ to L⁶, R¹ to R³, R^(a) and R^(b), each of the arylgroup, the fluorenyl group, the hetero ring group, the fused ring group,the arylene group and the fluorenylene group is further substituted withone or more substituents selected from a group consisting of deuterium;a nitro group; a nitrile group; a halogen group; an amino group; aC₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group; aC₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₆-C₂₀ aryl group; aC₆-C₂₀ aryl group substituted with deuterium; a fluorenyl group; aC₂-C₂₀ hetero ring group; a C₃-C₂₀ cycloalkyl group; a C₇-C₂₀ aryl alkylgroup; and a C₈-C₂₀ aryl alkenyl group, the substituents are allowed tobe bonded to form a ring, and each of the substituents is furthersubstituted with one or more substituents selected from a groupconsisting of deuterium; a nitro group; a nitrile group; a halogengroup; an amino group; a C₁-C₂₀ alkylthio group; a C₁-C₂₀ alkoxy group;a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₆-C₂₀ aryl group; a C₆-C₂₀ aryl group substituted with deuterium; afluorenyl group; a C₂-C₂₀ hetero ring group; a C₃-C₂₀ cycloalkyl group;a C₇-C₂₀ aryl alkyl group; and a C₈-C₂₀ aryl alkenyl group, and thesubstituents are allowed to be bonded to form a ring.
 2. The organicelectric element according to claim 1, wherein one of Ar¹ and Ar² isrepresented by formula 1-1, or one of Ar³ and Ar⁴ is represented byformula 1-1, or one of Ar¹ and Ar² is represented by formula 1-1, andone of Ar³ and Ar⁴ is represented by formula 1-1, or Ar¹ and Ar² arerepresented by formula 1-1, or Ar³ and Ar⁴ are represented by formula1-1, or one of Ar¹ and Ar² is represented by formula 1-1, and Ar³ andAr⁴ are represented by formula 1-1, or Ar¹ and Ar² are represented byformula 1-1, and one of Ar³ and Ar⁴ is represented by formula 1-1, orAr¹ to Ar⁴ are represented by formula 1-1.
 3. The organic electricelement according to claim 1, wherein the adjacent R¹s are bonded toeach other to form a ring, or the adjacent R²s are bonded with eachother to form a ring, or the adjacent R¹s are bonded to each other toform a ring, and the adjacent R²s are bonded with each other to form aring.
 4. The organic electric element according to claim 1, wherein X isO.
 5. The organic electric element according to claim 1, wherein X is S.6. The organic electric element according to claim 1, wherein one of Ar¹to Ar⁴ is represented by one of following Formulas 1-1a to 1-1e:

where R³ and c in the Formulas 1-1a to 1-1e are the same as defined inthe Formula 1-T of claim
 1. 7. The organic electric element according toclaim 1, wherein the compound represented by the Formula 1-T comprisesone of following compounds:


8. The organic electric element according to claim 1, wherein theorganic material layer comprises at least one of a hole injection layer,a hole transport layer, a light emitting auxiliary layer, a lightemitting layer, an electron transport auxiliary layer, an electrontransport layer, and an electron injection layer, and at least one ofthe hole injection layer, the hole transport layer, the light emittingauxiliary layer, the light emitting layer, the electron transportauxiliary layer, the electron transport layer, or the electron injectionlayer comprises in the organic material layer comprises the compoundrepresented by the Formula 1-T.
 9. The organic electric elementaccording to claim 1, wherein the organic material layer comprises afirst stack, a charge generating layer positioned on the first stack,and a second stack positioned on the charge generating layer, and thefirst stack comprises a first emitting layer, and the second stackcomprises a second emitting layer.